A mountainous landscape with autumn foliage.

Cottages in Town of Olive

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Town of Olive cottages

A wooden deck with a table and chairs, overlooking a grassy area with trees and a distant mountain range.

1. Mountain View escape

Mountain View escape
New Paltz
10.0 out of 10, Exceptional, (95 reviews)
"This was the best place I’ve stayed at. It felt more homely than actually being at home! Will find another reason to stay here very soon!"
United States
Liz C.
Mountain View escape
A wooden cabin surrounded by lush greenery and trees.

2. Streamside Cottage Half Mile to Town of Woodstock

Streamside Cottage Half Mile to Town of Woodstock
Woodstock
10.0 out of 10, Exceptional, (305 reviews)
"It was the perfect place for a weekend away from home! The location was only a few minutes from town and was the perfect size for a couple. Would definitely reccomend!"
United States
Kristen S.
The price is AED 592
AED 1,247 total
includes taxes & fees
4 Nov - 5 Nov
Streamside Cottage Half Mile to Town of Woodstock
A cottage with a wooden deck, a porch, and a staircase leading to the entrance.

3. Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks

Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks
Kerhonkson
9.6 out of 10, Exceptional, (18 reviews)
The price is AED 504
AED 899 total
includes taxes & fees
20 Oct - 21 Oct
Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks
Two red Adirondack chairs in a grassy field with a forest in the background.

4. Country Cottage with beautiful views and easy access to Catskills activities.

Country Cottage with beautiful views and easy access to Catskills activities.
Saugerties
9.8 out of 10, Exceptional, (22 reviews)
"Great location, amenities were exactly as described. "
United States
Eberechi A.
Country Cottage with beautiful views and easy access to Catskills activities.
A covered porch with a wooden bench, a wicker chair, and a sofa with cushions.

5. Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill

Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill
Catskill
9.8 out of 10, Exceptional, (21 reviews)
"The property was just as described, very private and cozy. We enjoyed the large balcony as well as the yard. There were also several nice hiking trails close by. Overall we were very happy with our stay."
United States
Ryan P.
The price is AED 450
AED 1,160 total
includes taxes & fees
3 Nov - 4 Nov
Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill
View from the fire pit

6. Charming Artist's Retreat

Charming Artist's Retreat
Saugerties
10.0 out of 10, Exceptional, (158 reviews)
"Such a beautiful spot! Convenient location that still felt like a peaceful retreat."
United States
Emily C.
Charming Artist's Retreat
A stone chimney, a red door, and a wooden bench.

7. Charming Cottage in the Heart of the Shawangunks

Charming Cottage in the Heart of the Shawangunks
Wallkill
10.0 out of 10, Exceptional, (31 reviews)
"The gatehouse was a perfect spot for a girls trip getaway. Secluded enough, but close to some local activities and restaurants! Cozy vibe and place had everything we needed!"
United States
Annelise A.
Charming Cottage in the Heart of the Shawangunks
A kitchen with white cabinetry, granite countertops, and a window with blinds.

8. Charming loft cottage in tranquil Germantown with WiFi, AC

Charming loft cottage in tranquil Germantown with WiFi, AC
Germantown
10.0 out of 10, Exceptional, (16 reviews)
"great location, clean & good communication with host."
United States
Kanna S.
Charming loft cottage in tranquil Germantown with WiFi, AC
A living room with a sofa, a coffee table with magazines, and a floor lamp.

9. Lily Cottage - a cozy accomodation moments from the beautiful Ashokan reservoir

Lily Cottage - a cozy accomodation moments from the beautiful Ashokan reservoir
Olivebridge
10.0 out of 10, Exceptional, (63 reviews)
"Clean and welcoming cottage in a great location. We would definitely stay there again. "
United States
Tanya R.
Lily Cottage - a cozy accomodation moments from the beautiful Ashokan reservoir
A small white house with a gabled roof, surrounded by lush greenery and trees.

10. The Cabin at Chichester in the Catskills Mountains

The Cabin at Chichester in the Catskills Mountains
Chichester
9.8 out of 10, Exceptional, (217 reviews)
"Great little cottage in the woods and not too far from town! Would stay here again!"
United States
Lisa S.
The Cabin at Chichester in the Catskills Mountains
A two-story building with a green roof, a covered porch, and a stone foundation.

11. Romantic cottage with hot tub . Close to hiking and breweries . Pet friendly!

Romantic cottage with hot tub . Close to hiking and breweries . Pet friendly!
Phoenicia
9.8 out of 10, Exceptional, (33 reviews)
"Just an overall amazing place to stay. We will return."
United States
Jennifer C.
Romantic cottage with hot tub . Close to hiking and breweries . Pet friendly!
A cabin with a deck, a fire pit, and a garage.

12. Relaxing Catskill Mountain Cottage.

Relaxing Catskill Mountain Cottage.
West Shokan
10.0 out of 10, Exceptional, (75 reviews)
"What a wonderful stay. "
United States
Emily C.
Relaxing Catskill Mountain Cottage.
A stone cabin with a wooden door, surrounded by trees.

13. ADORABLE CREEK COTTAGE Charming Original Details, Fireplace, Near Town, WiFi

ADORABLE CREEK COTTAGE Charming Original Details, Fireplace, Near Town, WiFi
Woodstock
9.8 out of 10, Exceptional, (97 reviews)
"Adorable cottage built in 1939. Close to town and well maintained."
United States
Julie Ann C.
ADORABLE CREEK COTTAGE Charming Original Details, Fireplace, Near Town, WiFi
A two-story house with a dark exterior, a yellow front door, and a wooden picket fence.

14. Private Woodstock Retreat • Walk to Town • Hot Tub

Private Woodstock Retreat • Walk to Town • Hot Tub
Woodstock
9.8 out of 10, Exceptional, (146 reviews)
"Excellent"
United States
Warren C.
Private Woodstock Retreat • Walk to Town • Hot Tub
A wooden deck with a table and chairs, a barbecue grill, and a blue umbrella.

15. Catskills Cottage w/ Deck, 7 Mi to Hunter Mtn

Catskills Cottage w/ Deck, 7 Mi to Hunter Mtn
Elka Park
9.4 out of 10, Exceptional, (20 reviews)
"We loved the stay at this cabin."
United States
Abha R.
Catskills Cottage w/ Deck, 7 Mi to Hunter Mtn
A wooden deck with picnic tables and benches, overlooking a forested area.

16. Charming Cottage Rental Near Woodstock Heated Pool, Fire Pit, Screened Porch

Charming Cottage Rental Near Woodstock Heated Pool, Fire Pit, Screened Porch
Woodstock
9.2 out of 10, Wonderful, (7 reviews)
"Beautiful property. The guest house is tucked back behind the main house with good privacy and separate entrance to the pool. The guest house has everything you need. The huge screened in porch was the highlight for me!"
United States
Kristin P.
Charming Cottage Rental Near Woodstock Heated Pool, Fire Pit, Screened Porch
A two-story building with a balcony, surrounded by a variety of colorful flowers and plants.

17. Herb Cottage-Historic Artist's Cottage in Woodstock: Wood Stove, Walk to Town!

Herb Cottage-Historic Artist's Cottage in Woodstock: Wood Stove, Walk to Town!
Woodstock
9.8 out of 10, Exceptional, (143 reviews)
"Great cozy place - awesome location."
United States
Eric F.
Herb Cottage-Historic Artist's Cottage in Woodstock: Wood Stove, Walk to Town!
A rustic wooden cabin with a porch, a front door, and a window.

18. Cozy 3-bedroom cottage in Hunter, NY

Cozy 3-bedroom cottage in Hunter, NY
Hunter
6.0 out of 10, (1 review)
"Host was responsive. House needed some cleaning and had some mildew smell. Host was receptive to fixing it."
United States
Lawrence S.
Cozy 3-bedroom cottage in Hunter, NY
A wooden deck with a white railing, surrounded by lush green trees.

19. Close to skiing in Windham and Hunter, hiking, lakes, 20+restaurants

Close to skiing in Windham and Hunter, hiking, lakes, 20+restaurants
Maplecrest
10.0 out of 10, Exceptional, (24 reviews)
"Great stay, lovely place, friendly host. Everything was perfect!"
United States
Taylor
The price is AED 1,319
AED 2,067 total
includes taxes & fees
18 Oct - 19 Oct
Close to skiing in Windham and Hunter, hiking, lakes, 20+restaurants
A wooden deck with rocking chairs and tables, surrounded by a wooden fence and trees.

20. Secluded Elka Park Cabin: Hot Tub & Fire Pit!

Secluded Elka Park Cabin: Hot Tub & Fire Pit!
3.0 star property
Tannersville
Secluded Elka Park Cabin: Hot Tub & Fire Pit!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Town of Olive Hotel Reviews

Quality Inn Hyde Park Poughkeepsie North

Quality Inn Hyde Park Poughkeepsie North

8/10 Good
"There is some wear and tear on the rooms, they could do with a refresh. But the room was clean. The breakfast was good - with waffles, eggs, sausage, yogurt fruit, juice and coffee. Close to nearby attractions like the FDR Library as well."
Ashley 1-night trip
Posted 6 hours ago
Quality Inn Hyde Park Poughkeepsie North

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